AUSTIN, Tex. — Holding his whiskey in one hand and his Stetson in the other, the opera’s hero — a tough stagecoach driver — offered an unhappy barmaid some advice in a strong, clear tenor voice.

“You could be anything,” sang the tenor, Holden Madagame.

He should know. Mr. Madagame, 28, is part of a new wave of transgender opera singers. Trained as a mezzo-soprano, he risked his singing career when he transitioned several years ago and began taking testosterone, which lowers and alters the voice — a voice he had spent years fine-tuning for opera, where success is measured in the subtlest of gradations.

“A couple of my singer friends were sort of like, you’re ruining your career, you’re ruining your life, the voice is everything,” he recalled recently. “And I thought, it’s not. I would rather enjoy my life, and pursue singing if it happens. I didn’t know if I’d be able to.”

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Holden Madagame, right, appearing in the opera “Good Country” in Austin, Tex., with the soprano Chang Liu.CreditJackie Lee Young for The New York Times

It turned out that he could. Now he is one of several transgender singers who are beginning to make their mark in the tradition-bound world of opera. Some, like him, found new voices, either with the help of hormones or through retraining. Others kept the voices they had built their careers on — even if it meant continuing to perform in the gender they had left behind. Now some are getting higher-profile roles — and upending preconceptions about voice and gender.

Opera itself is beginning to change: The most-produced new opera in North America in some recent seasons has been “As One,” a transgender coming-of-age story. This is happening as transgender rights are being debated by sports officials, in state legislatures and in the armed forces, where President Trump moved to ban transgender troops from serving.

As Mr. Madagame was singing in Austin this spring, a transgender woman, Lucia Lucas, was 450 miles north, at the Tulsa Opera in Oklahoma, rehearsing the title role in Mozart’s “Don Giovanni.” Ms. Lucas retained her powerful low baritone voice after her transition: Estrogen does not raise the voice the way testosterone lowers it.

“It would be great if I could just take estrogen and wake up and sing Brünnhilde,” she said. “It doesn’t work like that.”

In some respects, this generation of transgender singers is adding a new wrinkle to a very old tradition: Opera has been gender fluid since its beginnings. The earliest operas had boys’ roles sung by female sopranos, and both female and male roles were sometimes sung by castrati — men who were castrated before puberty to preserve their high voices.

When that practice ended, the high male roles they had sung were often taken by women. And many great composers, including Mozart and Strauss, wrote “trouser roles,” male parts created for women to sing. One of the most successful European transgender opera singers is Adrian Angelico, a 35-year-old Norwegian who kept his mezzo-soprano voice after transitioning in 2016, becoming one of the few men specializing in trouser roles.

We spent time with four of the artists at the forefront of this new wave.

Going From Mezzo to Tenor

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Mr. Madagame.CreditJackie Lee Young for The New York Times

At first, testosterone did not seem like an option.

Mr. Madagame, who was assigned female at birth, moved to Berlin after graduating from the University of Michigan, where he had studied singing, but things were not working out as planned.

“I got massively depressed. I just couldn’t sing,” he recalled. “And I kind of knew that it was about gender, but I didn’t want to admit it.”

By that point, he had put in years of hard work becoming a mezzo-soprano. A whole new voice could jeopardize it.

“Frankly, I did not have any experience with what would happen,” said Stephen West, one of his voice professors at Michigan, who remembered him as an exceptional mezzo.

Opera singers rely on their unamplified voices for their livelihoods, and they spend years perfecting their techniques — so they tend to be wary of anything that might strain or damage their voices. But Mr. Madagame had grown so unhappy that he decided to take the leap into the unknown.

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Holden Madagame sings in a recital before his transition.CreditCreditHolden Madagame

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Mr. Madagame appearing as a tenor in the opera “Good Country.”CreditCreditHolden Madagame

“I decided that if I’m not singing, and the only reason that I’m not taking testosterone is that I want to sing, then I should just take testosterone,” he said.

After the first few shots, he recalled, the timbre of his voice — its overall color and resonance — began to change. “At first, it’s not the actual pitches that are dropping,” he said, “but it’s like the overtones are lowering.”

Then came a period when his voice grew unsettled: “I had no singing voice — I had, like, an octave range,” he recalled. “It was terrifying. I thought, What if it stays like this?”

He felt better emotionally, but grew concerned when he still had trouble singing after the first few months. He began to wonder if he would be able to work again.

He returned to some of the easy Italian arias he had learned as a teenager, not too hard and not too high. But they were suddenly not so easy.

“They teach you a lot just by singing them,” he said. “I thought, Well, my voice just needs to be retrained to do these things. But at first I couldn’t even sing those.”

Stephanie Weiss, a voice teacher with a private studio, coached him as his voice settled, and saw him through tough early moments when his voice would crack. Mr. Madagame had a breakthrough while working on a Mozart aria. He was having trouble, as many young tenors do, gracefully reaching the high notes, Ms. Weiss remembered, so she gave him a few tips — including which vowels to hold as his voice climbed into his upper range.

Something clicked.

“He said, ‘Oh my God, I never thought I could make that sound,’” Ms. Weiss recalled.

It helped, she added, that Mr. Madagame had already developed a solid technique. “Now,” she said, “he really has found his voice — in every way.”

Soon Mr. Madagame, who now lives in Görlitz, a German town on the Polish border, began getting small roles with small companies in Germany and the United Kingdom. He was accepted by the Glyndebourne Academy, a program of the prestigious Glyndebourne Festival in England.

He dreams of singing Lensky, the doomed poet in Tchaikovsky’s “Eugene Onegin,” but he is mostly working now on smaller character tenor parts, not starring roles. “I’m 5-foot-2,” he noted — another casting challenge.

But it was a lead role that brought him to Austin. He starred in “Good Country,” an opera by the composer Keith Allegretti and the librettist Cecelia Raker that was based on the true story of Charley Parkhurst, a stagecoach driver who lived as a man but was discovered, after his death in 1879, to have been born a woman.

They wrote the part for a transgender singer — and after they cast Mr. Madagame, they tailored it with his voice in mind.

Changing ‘One Little Thing’

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Lucia Lucas.CreditShawn Brackbill for The New York Times

She entered the rehearsal room in her street clothes — striped top, silver flats, hair pulled back in a ponytail, a little lipstick on — and began singing one of the most toxically masculine characters in opera: the title role in Mozart’s “Don Giovanni.”

Mozart wrote a number of male roles for women to sing. Don Giovanni is not one of them. But as her booming, powerful baritone ricocheted off the walls, Ms. Lucas, 38, became the character — plotting his next seductions with relish and menace.

Her performances in Tulsa made headlines, and were the latest indication that her career was more than just getting back on track after she risked it by transitioning to female while working as a baritone for an opera company in Karlsruhe, Germany.

“It was always a question of, So, when is my career going to be done, so that I can transition?” she recalled in a recent interview in New York, explaining that she had felt disconnected from her birth gender since her childhood in Sacramento. “I never thought that they would coexist.”

But in 2013, she decided not to put off her transition any longer. She came out at the annual opera ball in Karlsruhe: Her wife, also a singer, wore a tuxedo, and Ms. Lucas wore a gown.

The company was initially supportive. “It was a good case study: Can somebody who is trans have a career in opera?” Ms. Lucas said. “I thought, Can I have a career after if I only change one little thing? It’s actually not something about the stage, it’s something personal. Because I’m going to continue singing baritone; I’m going to continue playing men on stage.”

Since hormones would not alter her voice, and retraining as a contralto seemed impractical, she remained a baritone. Now the vast majority of her stage roles are male — a gender she was uncomfortable with in life. But she said she had made peace with it.

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Ms. Lucas as Don Giovanni.CreditShawn Brackbill for The New York Times

“I’ll just go and put a beard on,” Ms. Lucas said, noting that she impersonates all kinds of characters onstage. “Clearly it is a disguise. It’s not bringing you back to an old life.”

When she had facial feminization surgery, she did not let her doctor do anything to her sinus cavity, nose or Adam’s apple.

“As much as I was putting my transition in front of my career,’’ she said, “I didn’t want him messing with anything that would mess with my voice.”

But after a while, her contract in Karlsruhe was not renewed, and she did not get called to auditions elsewhere that she would have expected in the past.

She grew more determined.

“Clearly my transition was important: It was more important than my career,” she said. “But now that I’ve done my transition, basically everything that I want to do, I’m like, Oh, no, I do love my career. I do want to keep my career. I’m going to fight for my career now.”

Her path to the Tulsa Opera began with an email from Tobias Picker, its artistic director and a composer who has written operas for the Metropolitan Opera and other major companies.

Mr. Picker was planning to write an opera based on “The Danish Girl,” David Ebershoff’s novel about one of the first people to attempt sex reassignment surgery, and he was looking for a transgender singer to appear in it. The idea appealed to Ms. Lucas: getting to premiere a new work by an important composer in which she would get to play a trans character.

But when Ms. Lucas came to New York to audition, and sang an aria from Verdi’s “Otello,” Mr. Picker decided to hire her for something much sooner.

“The Verdi was so astonishing that I thought, Well, it’s time to start casting ‘Don Giovanni’ anyway — so I asked her to do it,” Mr. Picker said.

Her appearance in Tulsa was an event. When an excerpt from a documentary that is being made about her was screened at a local art house, the Circle Cinema, Ms. Lucas told the audience that much of her work aimed to show people that being trans was not a big deal.

“I’m trying to show that being trans is not the story,” she told the crowd. “It’s sort of like anti-advocacy.”

Choosing to Wait on Hormones

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Liz Bouk.CreditJonno Rattman for The New York Times

“ID?” a transgender character asks a police officer in “Stonewall,” a new opera about the raid that helped spur the modern gay rights movement.

“I’d love to have an ID!” the character continues. “But the powers that be won’t give me one — at least not one that represents me.”

The line resonated with Liz Bouk, the mezzo-soprano singing it. Mr. Bouk is a transgender man who had only recently gotten a new driver’s license listing his sex as male.

“I felt like a teenage boy when I got that driver’s license,” he said. “After getting the driver’s license I went out and bought a pickup truck and learned how to drive stick shift.”

But Mr. Bouk’s transition, which came just as a hard-won career as a mezzo was finally beginning to blossom, involved difficult trade-offs. As much as he has sometimes longed to take hormones, he fears what they could do to his voice. So he decided to forgo them, and to keep playing what he calls “fiery women” and trouser roles on stage.

“If I’m working, if I’m singing,” he said, “can I stand the dysphoria of being in the wrong body, and being misgendered at the grocery store, or by people I don’t know?”

He changed his name from Elizabeth Anna to Liz (friends call him “Mr. Liz”) but put off a future change, possibly to John, so as not to confuse casting directors. He wears his blond hair long, but not as long as he used to. And he brings two head shots to auditions: one in a suit, labeled “Liz Bouk as himself,” and one in a dress, labeled “head shot for female roles.”

Since coming out as a man, he said, and feeling more at peace, his voice has improved. He has been working on shows about his journey. And he keeps getting work — and good reviews. But he sometimes has moments of yearning offstage, when he looks in the mirror.

“It would be great,” he said, “if my outsides matched my insides.”

Pushing Higher

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Breanna Sinclairé.CreditTalia Herman for The New York Times

“Please rise and remove your caps for our national anthem,” the announcer said shortly before the start of a 2015 Oakland A’s baseball game, “as performed by San Francisco Conservatory of Music graduate Breanna Sinclairé.”

Ms. Sinclairé raised a microphone and became what is believed to be the first transgender woman to sing the anthem at a major league game.

It made news around the world, and showed how far she had come since her darkest days, when she was briefly homeless and subjected to attacks on the streets of New York.

Ms. Sinclairé said that it was her earliest conviction that she did not feel comfortable in her body. That feeling carried into her singing, too.

“People kept pushing me to be the tenor, because I was tall,” Ms. Sinclairé said. “And I’m like, I don’t want to be no damn hero! I want to be the damsel in distress!”

After an unhappy stint at a bible college in Canada, she was admitted to the California Institute of the Arts — and saved enough money cutting grass to buy a Greyhound bus ticket to make the trip.

She decided to transition in her senior year at CalArts, and one of her teachers, Kate Conklin, encouraged her to try singing mezzo-soprano repertoire.

“We were working with what was already there.” Ms. Conklin said, noting that Ms. Sinclairé could already sing quite high.

Next came San Francisco, and its conservatory.

“We had never had anyone come in and audition for us who was transitioning,” said Ruby Pleasure, her teacher there. “And it was obvious that she was a diamond in the rough.”

Last New Year’s Eve, she appeared with the San Francisco Symphony. She continues to study, and is expanding into higher soprano roles. Next spring she will return to Canada to sing in an opera at the Against the Grain Theater in Toronto.

“I’m going to be in Toronto as my true self,” she said. “Singing soprano.”

Michael Cooper covers classical music and dance. He was previously a national correspondent; a political reporter covering presidential campaigns; and a metro reporter covering the police, City Hall and Albany. @coopnytimes•Facebook

A version of this article appears in print on , Section AR, Page 7 of the New York edition with the headline: Transgender and Singing Opera. Order Reprints | Today’s Paper | Subscribe